[go: up one dir, main page]

WO1998017468A1 - Mode de fabrication de vitres en verre feuillete de securite - Google Patents

Mode de fabrication de vitres en verre feuillete de securite Download PDF

Info

Publication number
WO1998017468A1
WO1998017468A1 PCT/DE1997/002409 DE9702409W WO9817468A1 WO 1998017468 A1 WO1998017468 A1 WO 1998017468A1 DE 9702409 W DE9702409 W DE 9702409W WO 9817468 A1 WO9817468 A1 WO 9817468A1
Authority
WO
WIPO (PCT)
Prior art keywords
film
silicon
silane
panes
polyvinyl alcohol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/DE1997/002409
Other languages
German (de)
English (en)
Inventor
Michael Henkel
Manfred Hoss
Bernhard Koll
Karl-Heinz Spiess
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huels Troisdorf AG
HT Troplast AG
Original Assignee
Huels Troisdorf AG
HT Troplast AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Huels Troisdorf AG, HT Troplast AG filed Critical Huels Troisdorf AG
Priority to DE19781146T priority Critical patent/DE19781146D2/de
Priority to AU53976/98A priority patent/AU5397698A/en
Publication of WO1998017468A1 publication Critical patent/WO1998017468A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10807—Making laminated safety glass or glazing; Apparatus therefor
    • B32B17/10816—Making laminated safety glass or glazing; Apparatus therefor by pressing
    • B32B17/10825—Isostatic pressing, i.e. using non rigid pressure-exerting members against rigid parts
    • B32B17/10834—Isostatic pressing, i.e. using non rigid pressure-exerting members against rigid parts using a fluid
    • B32B17/10844—Isostatic pressing, i.e. using non rigid pressure-exerting members against rigid parts using a fluid using a membrane between the layered product and the fluid
    • B32B17/10853—Isostatic pressing, i.e. using non rigid pressure-exerting members against rigid parts using a fluid using a membrane between the layered product and the fluid the membrane being bag-shaped
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10009—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
    • B32B17/10036—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising two outer glass sheets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10688—Adjustment of the adherence to the glass layers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • B32B17/10761—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing vinyl acetal
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds

Definitions

  • the invention relates to a method for producing composite security panes, consisting of at least two glass panes and an intermediate layer made of partially acetalized polyvinyl alcohol containing plasticizer, in a one-step, autoclave-free process.
  • Composite safety panes consisting of two glass panes and an adhesive film connecting the glass panes, preferably made of polybutyral (PVB), are used in particular as windscreens in motor vehicles, with a glass pane possibly being replaced by a plastic pane, primarily made of an amorphous polyamide, transparent PMMA, polycarbonate or polyester can be.
  • a glass pane possibly being replaced by a plastic pane, primarily made of an amorphous polyamide, transparent PMMA, polycarbonate or polyester can be.
  • silicate glass / silicate glass or silicate glass / plastic composites are used, where appropriate depending on their use, e. B. as composite armored glass, also multiple composites, ie composites that consist of more than two load-bearing layers, can be used.
  • a two-stage manufacturing process is generally used for the production of composite safety disks.
  • a so-called pre-composite consisting of the two glass panes and the adhesive film arranged between them, usually made of PVB, is produced.
  • This pre-composite is pressed in a second process step in an autoclave at temperatures of approx. 130 - 145 ° C and pressures of at least 11 bar to the actual composite safety disc.
  • This method is described, for example, in the introduction to EP 0 331 648 A2.
  • the water content of the PVB film used significantly influences the bond strength of the composite.
  • a water content of 0.40 to 0.55% by weight of the film is usually maintained - with very small tolerances. Due to the use of an autoclave, this known two-stage process is relatively complex and requires a high investment, so that it is unprofitable for small production quantities.
  • EP 0 331 648 A2 discloses an autoclave-free method of this type for producing composite safety disks.
  • the glass panes are glued together with the intermediate PVB film in an airtight, evacuated sack at elevated temperature by the external air pressure.
  • the PVB film used should have the lowest possible water content in order to avoid bubbles in the composite.
  • the adhesion that can be achieved between the layers of the composite, especially for the construction sector is not always sufficiently high.
  • DE 24 10 153 C3 discloses a method for adjusting the adhesive force of plasticized partially acetalized polyalcohols with silicon-functional and silicon-organofunctional silanes, the silicon-functional silanes reducing the adhesion and the silicon-organofunctional silanes increasing the adhesion.
  • the effect is not very high in normal processes.
  • the object of the present invention is a process for the production of composite safety glass, consisting of at least two glass panes and an intermediate layer of weichma ⁇ cher Reginam partially acetalized polyvinyl alcohol, m a single-stage, autoklavenUF method for jointing to provide that with sufficient process safety bubble-free laminated safety glass high liability, which in particular meet the requirements for the construction sector.
  • the invention achieves this object by using a plasticizer-containing partially acetalized polyvinyl alcohol film with a water content of less than 0.35% by weight, based on the mass of the film, and an effective content of an adhesion-increasing silicon-organofunctional silane in a one-step, autoclave-free process.
  • the partially acetalized polyvinyl alcohols can be prepared in a manner known per se by saponification of polyvinyl acetate and subsequent acetalization with aldehydes, such as, for. B. formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde and the like. the like getting produced. They usually still contain about 0.5 to 5 percent by weight, in particular about 0.5 to 1.2 percent by weight, of acetyl groups, calculated as vinyl acetate residues. Other polyvinyl esters of aliphatic acids with up to 9 carbon atoms can also be saponified and then acetalized. Partialized polyvinyl alcohol (PVB) is preferred. With regard to the polymers that can be used, reference is also made to DE 24 10 153 C3.
  • the film used for the process according to the invention contains plasticizers in amounts of preferably 20 to 40% by weight.
  • plasticizers that can be used are triethylene glycol di (2-ethylbutyrate), di-n-hexyl adipate (DHA) and preferably triethylene glycol bis-n-heptanoate (3G7).
  • the water content of the adhesive film is adjusted to a value of less than 0.35% by weight, preferably equal to or less than 0.30% by weight, in each case based on the mass of the film.
  • the water content to be observed according to the invention serves, on the one hand, to avoid bubbles in the finished composite safety panes, and together with the added silicon-organofunctional silanes, it also synergistically influences the adhesion between the adhesive film and the glass panes.
  • the silicon-organofunctional silanes used to increase the adhesion are known per se, for example from DE 24 10 153 C3, so that reference can be made to this document. While the addition of silicon organofunctional silanes which increase the adhesion in the customary autoclave process only brings about a moderate increase in the adhesion of film / glass, it has surprisingly been found that the same silane compounds have a multiple-fold effect when using an autoclave-free process. This is illustrated below using examples and comparative examples as well as the drawing.
  • Fig. 1 shows the pressure and temperature curve vs. Time according to Examples 1, 2 and Comparative Example 3
  • Fig. 2 shows the pressure and temperature curve vs. Time according to comparative examples 4 to 6
  • Fig. 3 is a schematic representation of an experimental device for a compression shear test.
  • a PVB adhesive film roughened on both sides is produced by a method according to EP 0 185 863 B1, Example 1.
  • Triethylene glycol bis-n-heptanoate (3G7) is used as the plasticizer.
  • a ⁇ -aminopropyltriethoxysilane is added to the plasticizer as silicon-organofunctional silane in an amount of 0.03% by weight, based on the mass of the film.
  • the water content of the PVB adhesive film was set at 0.29% by weight.
  • Two flat silicate glass sheets and the PVB adhesive film are then kuum vide in a single stage, autoklavenpli ⁇ Va, as described in EP 0331648 A2, processed into a laminated safety glass.
  • the process parameters were as follows: Table 1
  • Composite safety panes are produced by the same method as in Example 1, but using di-n-hexyl adipate (DHA) as a plasticizer.
  • DHA di-n-hexyl adipate
  • Composite safety panes are produced using the same procedure as in Example 1, but no silane is used.
  • the laminated safety glass thus produced are subjected to a standard compression shear test that allows a quantita tive ⁇ assessment of the glass / film adhesion.
  • the composite safety washers to be tested are clamped at an angle of 45 ° in a two-part test apparatus.
  • the obe ⁇ re half is exactly vertically subjected to a steadily increasing, downwardly directed force until tion to a Absche ⁇ within the test specimen, that is to be tested laminated safety glazing, comes.
  • the test device used for this is shown schematically in FIG. 3.
  • the test parameters were as follows:
  • the force exerted during shear is averaged from ten identical test specimens.
  • the standard deviation of the individual measurements is also calculated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Joining Of Glass To Other Materials (AREA)

Abstract

La présente invention porte sur un procédé de fabrication en une seule étape de vitres en verre feuilleté de sécurité, constituées d'au moins deux panneaux de verre et d'une couche intermédiaire d'alcool polyvinylique partiellement acétalisé et contenant du plastifiant. Selon le procédé sans autoclave, on utilise une feuille à base d'alcool polyvinylique partiellement acétalisé et contenant du plastifiant, avec une teneur en eau inférieure à 0,35 % en poids de la masse de feuille et avec une teneur utile en silane organosilicié fonctionnel qui accroît l'adhérence.
PCT/DE1997/002409 1996-10-21 1997-10-18 Mode de fabrication de vitres en verre feuillete de securite Ceased WO1998017468A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE19781146T DE19781146D2 (de) 1996-10-21 1997-10-18 Verfahren zur Herstellung von Verbundsicherheitsscheiben
AU53976/98A AU5397698A (en) 1996-10-21 1997-10-18 Method for producing laminated safety glass windows

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1996143404 DE19643404A1 (de) 1996-10-21 1996-10-21 Verfahren zur Herstellung von Verbundsicherheitsscheiben
DE19643404.1 1996-10-21

Publications (1)

Publication Number Publication Date
WO1998017468A1 true WO1998017468A1 (fr) 1998-04-30

Family

ID=7809342

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE1997/002409 Ceased WO1998017468A1 (fr) 1996-10-21 1997-10-18 Mode de fabrication de vitres en verre feuillete de securite

Country Status (3)

Country Link
AU (1) AU5397698A (fr)
DE (2) DE19643404A1 (fr)
WO (1) WO1998017468A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7704342B2 (en) 2001-12-27 2010-04-27 Solutia, Inc. Glass lamination process

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060231189A1 (en) * 2005-04-15 2006-10-19 Solutia, Inc. Low moisture polymer sheets
US7625627B2 (en) * 2005-12-30 2009-12-01 E.I. Du Pont De Nemours And Company Decorative polyvinyl butyral solar control laminates
RU2701931C1 (ru) * 2015-12-14 2019-10-02 Сэн-Гобэн Гласс Франс Способ безавтоклавного ламинирования многослойного стекла
WO2021254977A1 (fr) 2020-06-17 2021-12-23 Saint-Gobain Glass France Procédé de satrification d'une vitre composite sans un autoclave
WO2022186338A1 (fr) * 2021-03-04 2022-09-09 Ａｇｃ株式会社 Verre feuilleté et procédé de fabrication de verre feuilleté

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3625792A (en) * 1970-04-27 1971-12-07 Ppg Industries Inc Fabricating glass-plastic windows
US4144376A (en) * 1974-03-02 1979-03-13 Dynamit Nobel Aktiengesellschaft Process for the production of modified, partially acetalized polyvinyl alcohol films
EP0331648A2 (fr) * 1988-03-04 1989-09-06 Attilio Borgna Procédé de fabrication de verre laminé

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3909876A1 (de) * 1989-03-25 1990-09-27 Huels Troisdorf Formmasse zur herstellung von folien fuer verbundsicherheitsscheiben
DE4024330A1 (de) * 1990-07-31 1992-02-06 Huels Troisdorf Verfahren zur herstellung einer photochromen folie
JP3213979B2 (ja) * 1991-09-19 2001-10-02 株式会社ブリヂストン 合わせガラス

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3625792A (en) * 1970-04-27 1971-12-07 Ppg Industries Inc Fabricating glass-plastic windows
US4144376A (en) * 1974-03-02 1979-03-13 Dynamit Nobel Aktiengesellschaft Process for the production of modified, partially acetalized polyvinyl alcohol films
EP0331648A2 (fr) * 1988-03-04 1989-09-06 Attilio Borgna Procédé de fabrication de verre laminé

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7704342B2 (en) 2001-12-27 2010-04-27 Solutia, Inc. Glass lamination process

Also Published As

Publication number Publication date
DE19643404A1 (de) 1998-04-23
AU5397698A (en) 1998-05-15
DE19781146D2 (de) 1999-09-30

Similar Documents

Publication Publication Date Title
EP1042121B1 (fr) Feuille plastifiee constituee d'alcools polyvinyliques partiellement acetalises
DE69107117T2 (de) Zwischenlagen zur Verwendung in schallisolierenden Verbundgläsern.
DE69322432T2 (de) Zwischenschichtfolie für Verbundglas
EP1235683B1 (fr) Procede et film permettant de produire des vitres de securite composites
DE69935461T2 (de) Zwischenschichtfilm für Verbundglas und Verbundglas
EP2498989A1 (fr) Vitrages composites avec des feuilles contenant un plastifiant à faible tendance au fluage
DE69626442T2 (de) Zwischenschichtfilm und diesen enthaltendes Verbundglas
DE2646280C2 (de) Weichmacherhaltige Polyvinylbutyralfolien mit reduzierter Haftung an Glas
EP1430094B1 (fr) Feuille pour vitres de securite composites a auto-adhesivite reduite
DE2429032C2 (de) Zwischenschicht aus Polyvinylbutyral für Sicherheitsverbundglas
DE69501400T2 (de) Acrylat mischungen und verbundwerkstoffe die diese benutzen
EP0161583B1 (fr) Réduction de l'adhérence au verre de masses à mouler en polyvinylbutyral thermoplastiques contenant un plastifiant
WO1998017468A1 (fr) Mode de fabrication de vitres en verre feuillete de securite
EP0070394B1 (fr) Feuilles à base d'alcools polyvinyliques partiellement acétalisés contenant des plastifiants
DE2213982B2 (de) Sicherheitsverbundglas mit erhoehter durchschlagfestigkeit ohne verminderung der transparenz und alterungsbestaendigkeit und dafuer geeignetes zwischenmaterial
DE3850803T2 (de) Verfahren zur Herstellung von plastiziertem Polyvinylbutyral für die Leimung von Stützplatten auf eine Scheibe und hergestellte Produkte.
DE112019006121B4 (de) Folie für die Glaslaminierung und Verfahren zu ihrer Herstellung
EP0464070A1 (fr) Matiere de moulage pour la fabrication de films destines a des vitres de securite en verre feuillete
DE10064373A1 (de) Folie für Verbundsicherheitsscheiben mit verringerter Eigenklebrigkeit
DE68919381T2 (de) Verwendung einer thermoplastischen Zusammensetzung auf Polyvinybutyralbasis zur Befestigung von Stützplatten auf einer Glasscheibe.
DE1596875A1 (de) Verglasung in Form eines Schichtkoerpers aus zwei Glasscheiben und zwischengeordneter Kunststoffschicht
DE112020002617T5 (de) Verbundfolie zum verkleben und lichtdurchlässiges laminat mit dieser folie
DE112020003097B4 (de) Verbundfolie zum verkleben und lichtdurchlässiges laminat mit dieser folie
DE2302380A1 (de) Schichtglasscheiben fuer fahrzeuge
DE2410153C3 (de) Verfahren zur Einstellung der Haftkraft von weichmacherhaltigen teilacetalisierten Polyvinylalkohol-Folien an anorgansichen Gläsern und ihre Verwendung

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DE DK EE ES FI GB GE GH HU IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW AM AZ BY KG KZ MD RU TJ TM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH KE LS MW SD SZ UG ZW AT BE CH DE DK ES FI FR GB GR IE IT LU MC

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
REF Corresponds to

Ref document number: 19781146

Country of ref document: DE

Date of ref document: 19990930

WWE Wipo information: entry into national phase

Ref document number: 19781146

Country of ref document: DE

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA